{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,21]],"date-time":"2026-08-21T11:57:00Z","timestamp":1787313420432,"version":"build-2736575974"},"reference-count":21,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2025,2,6]],"date-time":"2025-02-06T00:00:00Z","timestamp":1738800000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Drug Testing and Analysis"],"published-print":{"date-parts":[[2025,9]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Synthetic cannabinoids, known as Spice or K2, emerged in Europe and the United States between 2005 and 2008, peaking in incidents by 2015 with severe health implications. In 2021, the identification of hexahydrocannabinol (HHC), a semisynthetic cannabinoid (SSC), led to regulatory control in more than 20 countries in Europe, several US states, and other jurisdictions. A 2024 study in the United States highlighted the diversity of semisynthetic cannabinoids in the US market. New entries of SSCs are increasingly available in the European market, often found as blends in consumer products. This highlights the growing complexity of their regulation and the potential public health risks due to limited toxicological data. The major ingredients, isolated from \u201cCB9\u201d, \u201ctresconol\u201d,\u00a0and \u201cCBx\u201d, were subjected to mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy. The major isolated ingredient of \u201cCB9\u201d was identified as [2\u2010(\n                    <jats:italic>E<\/jats:italic>\n                    )\u2010propen\u20101\u2010yl]\u2010\u0394\n                    <jats:sup>8<\/jats:sup>\n                    \u2010tetrahydrocannabinol\u2010acetate. The major ingredient of \u201ctresconol\u201d was identified as [2\u2010propen\u20102\u2010yl]\u2010\u0394\n                    <jats:sup>9<\/jats:sup>\n                    \u2010tetrahydrocannabinol, and the major ingredient of \u201cCBx\u201d was identified as [2\u2010propen\u20102\u2010yl]\u2010\u0394\n                    <jats:sup>8<\/jats:sup>\n                    \u2010tetrahydrocannabinol. These compounds have no available spectroscopic or chromatographic data, have never been identified in\n                    <jats:italic>Cannabis<\/jats:italic>\n                    plants, and cannot be identified by standard chromatographic forensic analytical methods, without the use of spectroscopic techniques due to the lack of reference standards. The products were complex mixtures of previously unknown synthetic cannabinoids lacking established safety profiles. These findings highlight the potential public health risks associated with unregulated SSCs, similar to the concerns raised during the 2015 Spice outbreak. The presence of these novel substances requires careful monitoring to prevent future health crises.\n                  <\/jats:p>","DOI":"10.1002\/dta.3866","type":"journal-article","created":{"date-parts":[[2025,2,6]],"date-time":"2025-02-06T03:45:51Z","timestamp":1738813551000},"page":"1594-1600","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Identification of Three Novel Tetrahydrocannabinol Analogs in the European Market"],"prefix":"10.1002","volume":"17","author":[{"given":"Evangelos","family":"Dadiotis","sequence":"first","affiliation":[{"name":"Laboratory of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy National and Kapodistrian University of Athens  Athens Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sotiris","family":"Mpakaoukas","sequence":"additional","affiliation":[{"name":"Laboratory of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy National and Kapodistrian University of Athens  Athens Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vangelis","family":"Mitsis","sequence":"additional","affiliation":[{"name":"Ekati Alchemy Lab SL  Barcelona Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Eleni","family":"Melliou","sequence":"additional","affiliation":[{"name":"Laboratory of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy National and Kapodistrian University of Athens  Athens Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0399-5344","authenticated-orcid":false,"given":"Prokopios","family":"Magiatis","sequence":"additional","affiliation":[{"name":"Laboratory of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy National and Kapodistrian University of Athens  Athens Greece"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,2,6]]},"reference":[{"key":"e_1_2_8_2_1","unstructured":"Poison Information and Prevention Education Repository https:\/\/piper.filecamp.com\/s\/i\/jbbjDA8ugqAZKl6C\/s\/v7pJtn8rpZegvPf6."},{"key":"e_1_2_8_3_1","unstructured":"Center for Disease Control and Prevention \u201cSynthetic Cannabinoids (Spice): An Overview for Healthcare Providers \u201dhttps:\/\/archive.cdc.gov\/www_cdc_gov\/nceh\/hsb\/envepi\/outbreaks\/sc\/healthcare.html (2023)."},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1056\/NEJMp1505328"},{"key":"e_1_2_8_5_1","unstructured":"European Union Drugs Agency \u201cNew Cannabinoid HHC in the Spotlight as Market Evolves \u201dhttps:\/\/www.euda.europa.eu\/news\/2023\/new\u2010cannabinoid\u2010hhc\u2010spotlight\u2010market\u2010evolves_en."},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja01866a040"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/dta.3519"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/dta.3777"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0140\u20106736(24)00307\u20106"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1089\/can.2023.0266"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11419\u2010023\u201000667\u20109"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1089\/can.2022.0126"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1159\/000536339"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jchemed.2c00966"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1186\/s42238\u2010021\u201000062\u20104"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.0c00436"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202302475"},{"key":"e_1_2_8_18_1","unstructured":"N.Wang R.Dubler andF.Ungemach \u201cFluorescence Polarization Immunoassay for Tetrahydrocannabinoids \u201d EU Patent No. EP0279308A2. \u201cAbbott Laboratories\u201d (1988)."},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1186\/s42238\u2010024\u201000226\u2010y"},{"issue":"11","key":"e_1_2_8_20_1","first-page":"1995","article-title":"Structure\u2010Activity Relationships in the Tetrahydrocannabinol Series. Modifications on the Aromatic Ring and It the Side\u2010Chain","volume":"22","author":"Edery H.","year":"1972","journal-title":"Arzneimittel\u2010Forschung"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tplants.2020.05.005"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/dta.3759"}],"container-title":["Drug Testing and Analysis"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/dta.3866","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,21]],"date-time":"2025-10-21T07:36:20Z","timestamp":1761032180000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/dta.3866"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,2,6]]},"references-count":21,"journal-issue":{"issue":"9","published-print":{"date-parts":[[2025,9]]}},"alternative-id":["10.1002\/dta.3866"],"URL":"https:\/\/doi.org\/10.1002\/dta.3866","archive":["Portico"],"relation":{},"ISSN":["1942-7603","1942-7611"],"issn-type":[{"value":"1942-7603","type":"print"},{"value":"1942-7611","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,2,6]]},"assertion":[{"value":"2024-08-12","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-01-28","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-02-06","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}